Methanol → HCID 19696260, compound

HRID 863529Notes

Reaction equation

HRID 863529 reaction equation
Cl.NC1C[C:10]2[C:5](=[CH:6][C:7]([Br:16])=[C:8]([NH2:15])[C:9]=2[N+:12]([O-:14])=[O:13])C1.[CH:17]([N:20]([CH:23]([CH3:25])[CH3:24])[CH2:21][CH3:22])([CH3:19])C.CCOC(C)=O.CO>CN(C=O)C>[NH2:15][C:8]1[C:9]([N+:12]([O-:14])=[O:13])=[C:10]2[C:5](=[CH:6][C:7]=1[Br:16])[CH2:24][CH:23]([N:20]1[CH2:17][CH2:19][CH2:22][CH2:21]1)[CH2:25]2

Participants

6

Reactant 4

HCID 887MethanolHCID 8857Ethyl AcetateHCID 81531DiisopropylethylamineHCID 19696169HCID 19696169, compound

Product 1

HCID 19696260HCID 19696260, compoundYield 30.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 2,5-diamino-6-bromo-4-nitroindane hydrochloride (1.5 g, 5 mmol), 1-4-dibromobutane (1.3 g, 6 mmol) and diisopropylethylamine (1.9 g, 15 mmol) in DMF (100 mL) was heated at 70° C. for 24 h. The solvent was evaporated and the residue taken up in methylene chloride:water. The aqueous layer was basified with 1N NaOH and back extracted. The combined organic layers were dried over sodium sulfate, filtered and evaporated to give a dark syrup. The purified product (0.5 g) was obtained from column chromatography (4:1 EtOAc:methanol).

Workup

  1. customThe solvent was evaporated
  2. extractionback extracted
  3. dry with materialThe combined organic layers were dried over sodium sulfate
  4. filtrationfiltered
  5. customevaporated
  6. customto give a dark syrup

Sources & evidence

ORD record
ord-9a9dc7471e8640d58926ac474b6159ff
Source dataset
uspto-grants-1998_02
Patent number
US05721234

Reaction notes

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